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Microsoft has plugged some key gaps in its 'new Outlook' for macOS, currently in preview and given a fresh update just a few days ago, but the product still has puzzling omissions that drive users back to the old version.

The revised Mac Outlook was first revealed at the Ignite event in late 2019. It appears to be a complete rebuild of the Mac email client, geared towards Office 365, but the question administrators will be pondering is whether important features in the existing Outlook will ever appear in the new one.

The history of Outlook on the Mac is inglorious. Microsoft and Mac go back a long way. Excel, for example, was a Mac application two years before it appeared on Windows. When it came to Outlook though, Mac users lost out. Outlook on Windows goes back to 1997, but the first full Mac version did not appear until Outlook 2011, and even that was not very good, slower than the Windows version and missing some features, such as Visual Basic for Applications (VBA).

VBA has never come to Outlook on the Mac, but a 2014 release was much improved, as Microsoft began to push the idea of Office 365 everywhere rather than keeping users hooked on Windows.

The new Outlook for the Mac in its first preview (click to enlarge)

Fast-forward to today, and there is not that much missing in Outlook 365 for Mac versus Windows, VBA aside.

All that is set to change with the latest new Outlook Mac as the pendulum swings away from making the Mac Outlook close to the Windows one, and towards giving Mac users a more distinct experience. It is also a matter of protocols. The existing Outlook Mac uses Exchange Web Services (EWS) which is being phased out.

Outlook on Windows generally uses MAPI over HTTP, perhaps the nearest thing to a native Exchange protocol. Microsoft is not happy with either and for its 'modern' mail client in Windows 8 and Windows 10 it developed a new sync protocol. In the past this was sometimes called Hx but it seems now to go by the name Microsoft Sync.

Outlook for Mac provides a way on how to subscribe and unsubscribe to/from IMAP folders. Open Outlook application - Tools - IMAP folders. Select Kerio Connect IMAP account - select the necessary folders - click Subscribe. The selected folders are being shown under the Kerio IMAP account folder list.

  • All Macs on the network using Outlook with their email stored on an IMAP mail server. We'd like to migrate them to a full Office 365 solution with their mail on O365 Exchange. I was thinking of using something like Bit Titan to automate the migration, but because IMAP doesn't store the contacts etc, I thought I'd just export each profile to PST.
  • Microsoft Outlook for Mac Add Your Gmail Account to Outlook 2011 Mac Using IMAP. To set up your Outlook client to work with Gmail: Enable IMAP in Gmail; Sign in to Gmail. Click the gear icon in the upper-right and select Gmail settings at the top of any Gmail page. Click Forwarding and POP/IMAP; Select Enable IMAP.

When Microsoft acquired Accompli in 2014, whose product became Outlook Mobile, it used its own protocol but that too now uses Microsoft Sync. According to presentations at Ignite 2019, this new sync protocol is designed specifically for mail-related data and makes the best even of poor connections, prioritising recent data.

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The move from EWS to Microsoft Sync enables new features and improved performance, and no longer downloads the entire mailbox to the local machine. System requirements are for macOS 10.14 Mojave and Office 365, Outlook.com or Gmail email accounts.

The snag with a rebuilt Outlook for Mac is that having nearly caught up with Windows Outlook, it is now far behind in terms of features. It is in preview and some will reappear, but it is unlikely to be the full set. It hardly qualifies as a mail client in its current incarnation, with no support for standard protocols like POP3 and IMAP, nor any way of connecting to on-premises Exchange.

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'We don't support on-prem yet but it's going to come soon,' said Microsoft in November 2019; six months on it is not there yet. On the plus side, it not only looks pretty, with full support for the Mac's Dark Mode on Catalina, but also performs well, with a fluidity that frankly feels unusual in a Mac Outlook product.

Features of the new Outlook for Mac include a new unified inbox view that avoids clicking between accounts, if you have several configured. You can now reply to emails inline ('nested compose'), a convenience feature that has been in Windows Outlook for some time. There is a new 'ignore conversation' option. Creating meetings uses a new simplified dialogue that you can expand as needed.

As for the new features added in the June update, these include add-in support (a big deal), sensitivity labels for classifying confidential data, a People view for managing contacts, an option to create an event directly from an email, read receipts, and a 'coming soon' promise of the ability to open shared calendars and to encrypt emails with S/MIME.

Microsoft's Forthcoming Outlook For Mac Should Boost WFH ...

The actual preview release did not quite live up to the promise. In particular, the People view is not yet enabled, thanks to some last-minute bug that was discovered. One gets the new Outlook by signing up to the Office 'Insider Fast' channel, and after the new version downloads and installs, one can switch back and forth by toggling a 'New Outlook' switch. If the user attempts to use a feature such as the People view, a message pops up inviting the user to switch back, wrecking the fluid experience but that is what one gets for trying a preview.

The current preview is not fully usable, but fortunately switching back is quick

The problem of Outlook on Windows being different from Outlook on Mac will get worse

Microsoft has not specified a release date for the new Outlook Mac but a few things are clear. First, it will be the best Outlook yet, perhaps on any platform, in terms of appearance and design. This is not a high bar: Outlook on Windows is a mess from a user interface perspective, and has dialogues buried within that have not changed for decades. Performance also looks promising.

Second, Outlook Mac will be focused on cloud, especially Office 365, though it also already has good support for Google mail. Teams integration will also be strong and Microsoft has demonstrated features like converting an event to a Teams meeting, handy in times of lockdown.

Lastly, the problem of Outlook on Windows being different from Outlook on Mac will get worse. What if Microsoft replaces the Windows version with a similarly rebuilt product? Perhaps it will; but the difficulty is that Outlook is baked into the Windows ecosystem and forms part of workflows, some automated with COM technology, that will break if Microsoft replaces it. Custom add-ins, VBA projects, ancient APIs that remain for legacy reasons, all mean this will be a tricky application to replace.

Creating a meeting in the new Outlook Mac: just drag in the calendar and this simple dialog pops up

Outlook on Windows is perhaps the most annoying of Microsoft's Office products, yet the job it does is a critical one, bringing together email, calendar and tasks, and providing collaboration features like shared calendars and contacts. Some legacy features, like Exchange public folders, made their way into Office 365 where they have become something of a burden to Microsoft.

The new Outlook for Mac, when it comes out of preview, will represent Microsoft's current thinking on how Outlook should look and behave in the cloud era, but it will be some time before that can apply in Windows as well. ®

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Outlook for Mac facilitates offline working in an Exchange environment. Synchronization between the server and client application is done so that whenever there is any modification in the Server-side or client-side, the change gets updated on the other side. Sometimes, this synchronization process gets affected partially or fully. Due to this, mailboxes are not updated on the server-side as well as on the client-side.

Prominent Reasons Behind this Synchronization Issue

Many Outlook for Mac users face this issue, and so we need to realize the causes behind it. We have stated them here:

  • Offline Mode: Your Outlook for Mac is in Offline Mode
  • Failed to Connect: You failed to connect Outlook for Mac with the Exchange Server
  • Cache Issue: Your Outlook Cache is corrupted
  • Settings: Settings are not accurately configured
Fixing “Outlook for Mac not syncing with Exchange Server” issue

Now, as you have got the main reasons behind the issue, we will provide you some ways to get out of this issue.

Read Also: What Outlook for Mac Users can do when their Exchange mailbox is full?
  1. Check Offline Mode
    It is the most basic check that you can perform before pursuing any other method. Go to the Outlook menu and check if the Work Offline option is selected or not. If selected, unselect it and check if the synchronization is better now.
  2. Rebuild the Outlook for Mac File
    To fix this issue, you should perform the troubleshooting as explained here.
    Firstly, close all the Outlook for Mac related processes currently running on the system. Take a backup of the Identities folder of Outlook for Mac in C drive. Then click on Outlook application with Alt key on hold to start the Microsoft Database Utility app. Here, select the identity which you want to recreate and click the Rebuild option to create it. Wait until the process gets completed.
  3. Clear Cache in Outlook
    This method works when any specific folder is not synchronizing, but the rest of the Exchange folders are synchronizing with the Outlook. Here is the fix.
    First, ensure that there is a connection between Outlook for Mac and Exchange Server. Right-click on the respective Exchange folder which is not synchronizing and click on the Properties option. Now, switch to the General tab and click on the option Empty Cache. Next, check if the folder is synchronized and new items are received in it.
  4. Confirm Exchange Connectivity
    The issue can be due to error in connection of Outlook with the correct Exchange Server. You should check it once to confirm if this is the issue. Follow this process:

    Go to Tools > Accounts in your Outlook for Mac and check over the Exchange Account. If there is an orange indicator against the added Exchange account, then it means there is some issue with it. You can try disconnecting it and re-configuring it. Try connecting it with Outlook on the web and check the status of Exchange Server now. If everything is fine, connect the desired server again.

The above methods are easy and can solve the synchronization issue between Outlook for Mac and Exchange Server. You can give these solutions a try and get rid of that unwanted situation quickly.

Microsoft’s New Outlook For Mac Design Launches In October ...

How to Retrieve Inaccessible Outlook for Mac Data?

How To Fix Mac Outlook 2011 Slow IMAP Mail Access

If you are still not able to fix the issue with your Outlook for Mac data file, you can think of converting the OLM file to PST and recover its data. For this, we bring the most promising OLM Converter tool – Kernel for OLM to PST Converter tool, which converts OLM file to Outlook 2019, 2016 & 2013. It also allows users to make secure migration from OLM to Exchange Server and cloud-based platform of Office 365. The tool provides many filter options for users to move only specific data to the destination. Also, it provides complete support to all Outlook for Mac versions including Outlook 2016 for Mac.

You may better understand the OLM to PST conversion process by going through the steps of the tool.

  1. Run Kernel OLM to PST Converter and use Browse or Search (for automatic search in the selected system drive) option to add the desired number of OLM files for conversion purposes. Click Next.
  2. After scanning the files, select any mailbox item and view its preview. Now, click the Save option.
    Note 1: You can save file items in multiple formats by right-clicking and selecting the required option.
    Note 2: With the Find option on the Toolbar, you can perform a deep search for any mailbox item using multiple filters and options.
  3. Choose PST File (MS Outlook) option. Click Next.
  4. Add filters like email metadata (From, To, Subject), Item Type, and Date Range as required and click Next.
  5. To manage the converted PST file size, you can use the Split option and also can add a prefix to the store name.
  6. Browse and add the saving path location for the converted PST file and click Finish.
  7. The conversion process will get started and soon completes with a confirmation message.
    So, conversion of OLM to PST file is quite handy with the Kernel OLM to PST Converter software.

Final Words

Due to the Exchange synchronization issue, Outlook for Mac users may not have the updated information in their mailboxes. This issue can be fixed in many ways. However, if all these methods fail to fix the issue, they can think of recovering Outlook for Mac data using an OLM to PST converter.

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